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Chemical Structure| 1025451-57-3 Chemical Structure| 1025451-57-3

Structure of 1025451-57-3

Chemical Structure| 1025451-57-3

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Product Details of [ 1025451-57-3 ]

CAS No. :1025451-57-3
Formula : C20H24N2S3Sn2
M.W : 626.03
SMILES Code : C[Sn](C1=CC=C(C2=CC=C(C3=CC=C([Sn](C)(C)C)S3)C4=NSN=C42)S1)(C)C
MDL No. :MFCD28049209
InChI Key :INHYKPMJJAWZKY-UHFFFAOYSA-N
Pubchem ID :58153009

Safety of [ 1025451-57-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H300+H310+H330-H410
Precautionary Statements:P501-P273-P260-P270-P262-P271-P264-P280-P284-P391-P361+P364-P301+P310+P330-P302+P352+P310-P304+P340+P310-P403+P233-P405
Class:6.1
UN#:3146
Packing Group:

Computational Chemistry of [ 1025451-57-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 27
Num. arom. heavy atoms 19
Fraction Csp3 0.3
Num. rotatable bonds 4
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 130.0
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

110.5 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.0
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

8.15
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

6.24
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

4.1
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

7.58
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

5.21

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-9.11
Solubility 0.000000483 mg/ml ; 0.0000000008 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-10.33
Solubility 0.0000000294 mg/ml ; 0.0 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Insoluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-8.99
Solubility 0.000000642 mg/ml ; 0.000000001 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

Low
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

Yes
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

Yes
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-4.33 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

1.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

1.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<2.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

3.83

Application In Synthesis of [ 1025451-57-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 1025451-57-3 ]

[ 1025451-57-3 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 1066-45-1 ]
  • [ 165190-76-1 ]
  • [ 1025451-57-3 ]
YieldReaction ConditionsOperation in experiment
89%
Stage #1: With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2 h;
Stage #2: at -78 - 20℃; for 12 h;
To a solution of 2,2,6,6-tetramethylpiperidine (4.22 g, 29.9 mmol) in THF (85 mL), n-butyllithium hexane solution (1.6 M, 18.69 mL, 29.9 mmol) was added at a temperature of 78 °C. Afterstirring for 1 h at 78 °C, the reaction mixture was warmed up to room temperature, and then cooled again to 78 °C, followed with the dropwise addition of a solution of 4,7-di(2-thiophene)-2,1,3-benzothiadiazol (3.45 g, 11.5 mmol) in THF (35 mL). After stirringat 78 °C for 2 h, Me3SnCl hexane solution (1.0 M, 29.9 mL, 29.9 mmol) was added and the reaction mixture was warmed up to room temperature. After stirred for 12 h, the reaction was quenched with deionized water and extracted with diethyl ether. The organic phase was washed with deionized water several times, dried over MgSO4, and evaporated to dryness. The residue was subjected to recrystallization from acetone, affording 4,7-Di(2-trimethylstannylthiophen-5-yl)-2,1,3-benzothiadiazole (6.38 g) as orange crystals with a yield of 89percent.
75%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1 h;
Stage #2: at 20℃;
A solution of compound 1 (0.77 g, 2.56 mmol) in anhydrousTHF (40 mL) was added dropwise at −78 °C to 2.0M lithiumdiisopropylamine (LDA, 3.20 mL, 6.4 mmol). After stirring for 1 h at−78 °C, trimethyltin chloride (7.69 mL, 7.68 mmol, 1M in hexanes)was added dropwise to the reaction mixture. Subsequently, the reactionflask was warmed to room temperature and stirred overnight. The reactionmixture was quenched with distilled water and extracted withdiethyl ether. The organic layer was washed twice with brine and driedover MgSO4. After drying the extracts, the obtained residue was purifiedby recrystallization from ethanol to yield red crystals. Yield: 75percent(1.2 g). 1H NMR (300 MHz, CDCl3, ppm): δ 8.18 (d, J=3.3 Hz, 2H),7.87 (s, 2H), 7.30 (d, J=3.6 Hz, 2H), 0.43 (s, 18H).
References: [1] Journal of Organic Chemistry, 2015, vol. 80, # 3, p. 1828 - 1840.
[2] Polymer, 2015, vol. 59, p. 57 - 66.
[3] Journal of Materials Chemistry C, 2017, vol. 5, # 27, p. 6891 - 6898.
[4] Dyes and Pigments, 2018, vol. 156, p. 318 - 325.
[5] Journal of Polymer Science, Part A: Polymer Chemistry, 2016, vol. 54, # 4, p. 525 - 531.
[6] New Journal of Chemistry, 2016, vol. 40, # 2, p. 1655 - 1662.
[7] Chemistry of Materials, 2012, vol. 24, # 21, p. 4123 - 4133.
[8] RSC Advances, 2017, vol. 7, # 33, p. 20440 - 20450.
  • 2
  • [ 15155-41-6 ]
  • [ 1025451-57-3 ]
References: [1] Chemistry of Materials, 2012, vol. 24, # 21, p. 4123 - 4133.
[2] Journal of Materials Chemistry C, 2017, vol. 5, # 27, p. 6891 - 6898.
  • 3
  • [ 273-13-2 ]
  • [ 1025451-57-3 ]
References: [1] RSC Advances, 2017, vol. 7, # 33, p. 20440 - 20450.
 

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